132785-20-7Relevant academic research and scientific papers
Stereocontrolled synthesis of β-hydroxyphenylalanine and β- hydroxytyrosine derivatives
Easton,Hutton,Roselt,Tiekink
, p. 7327 - 7340 (2007/10/02)
Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-β-hydroxy-α- amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group. tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.
